Sodium hydride → HCID 66747768、化合物

HRID 1405914

反応式

HRID 1405914 の反応式
[H-].[Na+].[NH2:3][C:4]1[C:9]([O:10][C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([OH:21])=[CH:18]3)=[CH:13][CH:12]=2)=[CH:8][CH:7]=[CH:6][N:5]=1.CC1C=CC(S(O[CH2:33][C:34]([F:37])([F:36])[F:35])(=O)=O)=CC=1.[Cl-].[NH4+]>CS(C)=O.C1COCC1>[F:35][C:34]([F:37])([F:36])[CH2:33][O:21][C:17]1[CH:18]=[C:19]2[C:14]([CH:13]=[CH:12][C:11]([O:10][C:9]3[C:4]([NH2:3])=[N:5][CH:6]=[CH:7][CH:8]=3)=[CH:20]2)=[CH:15][CH:16]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 667477657-[(2-Aminopyridin-3-yl)oxy]naphthalen-2-ol

生成物 1

HCID 66747768HCID 66747768、化合物収率 16.9%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
120 °C

実験手順

To a mixture of sodium hydride (60%, 116 mg), 7-[(2-aminopyridin-3-yl)oxy]naphthalen-2-ol (477 mg) and dehydrated THF (10 mL) was added a mixture of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (370 mg) and dehydrated THF (5 mL) at room temperature. The reaction mixture was stirred at 70° C. over the weekend, DMSO (10.00 mL) was added and the mixture was stirred at 120° C. for 1 hr. The reaction mixture was added to a saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (82 mg) as a pale-yellow viscous product.

後処理

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-a548c896f8784660890d61b38ebc4f1b
出典データセット
uspto-grants-2014_12
特許番号
US08916551B2

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